Supramolecular Polymerization of Triarylamine-Based Macrocycles into Electroactive Nanotubes
Flavio Picini, Susanne Schneider, Odile Gavat, Andreas Vargas Jentzsch, Junjun Tan, Mounir Maaloum, Jean‐Marc Strub, Shoichi Tokunaga, Jean‐Maríe Lehn, Émilie Moulin, Nicolas Giuseppone
Abstract
A S6-symmetric triarylamine-based macrocycle (i.e., hexaaza[16]paracyclophane), decorated with six lateral amide functions, is synthesized by a convergent and modular strategy. This macrocycle is shown to undergo supramolecular polymerization in o-dichlorobenzene, and its nanotubular structure is elucidated by a combination of spectroscopy and microscopy techniques, together with X-ray scattering and molecular modeling. Upon sequential oxidation, a spectroelectrochemical analysis of the supramolecular polymer suggests an extended electronic delocalization of charge carriers both within the macrocycles (through bond) and between the macrocycles along the stacking direction (through space).